EP0107888B2 - Polyester et son utilisation comme revêtement en poudre - Google Patents

Polyester et son utilisation comme revêtement en poudre Download PDF

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Publication number
EP0107888B2
EP0107888B2 EP83201538A EP83201538A EP0107888B2 EP 0107888 B2 EP0107888 B2 EP 0107888B2 EP 83201538 A EP83201538 A EP 83201538A EP 83201538 A EP83201538 A EP 83201538A EP 0107888 B2 EP0107888 B2 EP 0107888B2
Authority
EP
European Patent Office
Prior art keywords
powder coating
polyester
acid
coating according
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP83201538A
Other languages
German (de)
English (en)
Other versions
EP0107888B1 (fr
EP0107888A1 (fr
Inventor
Eimbert Gerrit Belder
Robert Van Der Linde
Jan Schippers
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Resins BV
Original Assignee
DSM Resins BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19840494&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0107888(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by DSM Resins BV filed Critical DSM Resins BV
Priority to AT83201538T priority Critical patent/ATE20530T1/de
Publication of EP0107888A1 publication Critical patent/EP0107888A1/fr
Publication of EP0107888B1 publication Critical patent/EP0107888B1/fr
Application granted granted Critical
Publication of EP0107888B2 publication Critical patent/EP0107888B2/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers

Definitions

  • the application relates to a powder coating of which the binding agent contains a homogeneous mixture of triglycidyl isocyanurate and a polyester containing carboxyl groups, which polyester is based on a substantially aromatic dicarboxylic acid mixture and on a substantially aliphatic diol mixture.
  • Polyesters containing carboxyl groups for use in powder paints are already known from the prior art and in practice these are processed to binding agents for powder coatings in a combination of at least 7 % by weight triglycidyl isocyanurate (TGIC) and consequently at most 93 % by weight polyester.
  • TGIC triglycidyl isocyanurate
  • the present invention now provides powder coatings based on binding agents which are improved with respect to one or several of the aforementioned problems.
  • the powder coating according to the invention is characterized in that the mixture contains between 1.4 and 5.3 % by weight triglycidyl isocyanurate and from 94.7 to 98.6 % by weight of a polyester containing carboxyl groups with the following combination of properties: an acid number between 12 and 24 mg KOH/g, a hydroxyl number that is smaller than 15 mg KOH/g, a theoretical number-average molecular weight between 4,500 and 12,500, a glass transition temperature between 40°C and 85°C and a viscosity of 430-1300 dPas at 165°C.
  • the weight percentage of the triglycidylisocyanurate is between 1.6 and 4.9 % by weight and the weight percentage of the polyester is between 95.1 and 98.4 % by weight.
  • Conspicuous therein is especially the relatively high molecular weight of the polyester, and it is quite surprising that in spite of this higher molecular weight an excellent flow of the powder coating is obtained.
  • the polyester resin contains relatively little low molecular material, as a result of which a better powder stability arises.
  • the low lower limit of the glass transition temperature range is also conspicuous. The greater clearness in combination with the excellent flow of the coating which the polyester/epoxy binding agent systems according to the invention yield makes these systems particularly suitable as top-coating for automobiles.
  • the theoretical number-average molecular weight of the polyester is preferably 5,500-10,500, and the glass transition temperature is preferably between 50 and 70°C.
  • the average carboxyl functionality of the polyester is in the range of 2 to 3, preferably between 2.2 and 2.8, more particularly between 2.2 and 2.5.
  • the polyesters containing carboxyl groups may be prepared, in manners which are known per se, substantially from aromatic polycarboxylic acids, such as phthalic acid, isophthalic acid, terephthalic acid, benzene-1,2,4-tricarboxylic acid, pyromellitic acid, trimesic acid, 3,6-dichlorophthalic acid, tetrachlorophthalic acid, or from the anhydrides, acid chlorides or lower alkyl esters thereof, in as far as these are obtainable.
  • the carboxylic acid component consists to at least 50, preferably at least 70 mol.% of aromatic dicarboxylic acids, particularly isophthalic acid and/or terephthalic acid.
  • aliphatic diols such as ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,2-diol, butane-1,4,-diol, 2,2-dimethylpropanediol-1,3 (neopentyl glycol), hexane-2,5-diol, hexane-1,6-diol, 2,2-[bis-4(hydroxycylclohexyl)]-propane, 1,4-dimethylolcyclohexane, diethylene glycol, dipropylene glycol and 2,2-bis-[4-(2-hydroxyethoxy)phenyl]-propane, and smaller amounts of polyols, such as glycerol, hexanetriol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane and tris-(2-hydroxyethyl)iso
  • cycloaliphatic and/or acyclic polycarboxylic acids may be used as polycarboxylic acids, for example tetrahydrophthalic acid, hexahydroendomethylenetetrahydrophthalic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dimeric fatty acid, adipic acid, succinic acid and maleic acid, in amounts of at most 30 mol.%, preferably to a maximum of 20 mol.% of the total amount of carboxylic acids.
  • hydroxycarboxylic acids and/or optionally lactones may be used, e.g.
  • Monocarboxylic acids such as benzoic acid, tert.-butylbenzoic acid, hexahydrobenzoic acid and saturated aliphatic monocarboxylic acids may also be added in minor amounts during the preparation.
  • polyesters are prepared, in manners known per se, by esterification or interesterification, whether or not in the presence of conventional catalysts, such as e.g. dibutyl-tin oxide or tetrabutyl titanate, whereby, through a suitable choice of heating conditions and of the COOH/OH ratio, end products are obtained of which the acid number lies between 12 and 24 mg KOH/g.
  • catalysts such as e.g. dibutyl-tin oxide or tetrabutyl titanate
  • a compound having 4 or more methylene groups optionally substituted with lower alkyl groups e.g. adipic acid, pentanediol-1,5 or dipropylene glycol.
  • cross-linking agent triglycidyl isocyanurate is used.
  • TGIC having an epoxy content of at least 9.3 equivalents per kg.
  • the amount of triglycidyl isocyanurate that is used in combination with the polyester is dependent on the acid number of the polyester and lies between 0.8 and 1.2, preferably between 0.9 and 1.1 equivalent epoxy per equivalent carboxyl. This means that between 1.4 and 5.3 % by weight, preferably between 1.6 and 4.9 % by weight TGIC and consequently 94.7 to 98.6 % by weight preferably 95.1 to 98.4 % by weigth polyester are used. It is quite surprising that, with the use of these small amounts of TGIC, nevertheless well-cured coating layers are obtained.
  • the polyester and the TGIC are homogeneously mixed, preferably in the melt, by means of an extruder.
  • the usual additives are added before the mixing. This concerns especially flowing aids, curing catalysts and optionally pigments and/or fillers.
  • the mixture thus obtained is subsequently ground and sieved, and this powder paint is then applied by means of an electrostatic spraying apparatus and thereafter cured in a stoving oven for 10 to 30 minutes at temperatures of between 160 and 200°C.
  • the coating layer thus obtained exhibits an excellent combination of gloss, flow, clearness and mechanical properties, with the powder paint having a very good powder stability both in chemical and physical respect.
  • polyester resins according to the invention were prepared of which the charge composition, acid number, OH number, viscosity at 165°C, glass transition temperature and theoretical number-average molecular weight are given in Table 1.
  • Example 2 powder coatings were prepared starting from the polyester resins according to Examples 2A-10A.
  • the compositions and the test results of these powder coatings are given in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Laminated Bodies (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Epoxy Resins (AREA)

Claims (8)

  1. Revêtement en poudre dont l'agent liant contient un mélange homogène d'isocyanurate de triglycidyle et un polyester contenant des groupes carboxyle, polyester qui est à base d'un mélange d'acides dicarboxyliques sensiblement aromatiques et d'un mélange de diols sensiblement aliphatiques, caractérisé en ce que le mélange homogène contient de 1,4 à 5,3% en poids d'isocyanurate de triglycidyle et de 94,7 à 98,6% en poids d'un polyester contenant des groupes carboxyle, avec la combinaison suivante de propriétés :
    un indice d'acide de 12 à 24 mg KOH/g, un indice d'hydroxyle inférieur à 15 mg KOH/g, une masse moléculaire moyenne théorique en nombre de 4500 à 12500, une température de transition vitreuse de 40 à 85°C et une viscosité de 430 à 1300 dPas à 165°C.
  2. Revêtement en poudre selon la revendication 1, caractérisé en ce que le polyester présente une masse moléculaire moyenne théorique en nombre de 5500 à 10500.
  3. Revêtement en poudre selon la revendication 1 ou 2, caractérisé en ce que la température de transition vitreuse du polyester est de 50 à 70°C.
  4. Revêtement en poudre selon l'une quelconque des revendications 1 à 3, caractérisé en ce que la fonctionnalité carboxylique moyenne est de 2,2 à 2,8.
  5. Revêtement en poudre selon l'une quelconque des revendications 1 à 4, caractérisé en ce que le polyester contient un composé comportant au moins 4 groupes méthylène facultativement substitués en une proportion jusqu'à 15 moles%.
  6. Revêtement en poudre selon l'une quelconque des revendications 1 à 5, caractérisé en ce que le pourcentage en poids de l'isocyanurate de triglycidyle est compris entre 1,6 et 4,9%.
  7. Procédé de revêtement électrostatique d'un substrat avec un revêtement en poudre et durcissement du revêtement en poudre, caractérisé en ce qu'on utilise un revêtement en poudre selon l'une quelconque des revendications 1 à 6.
  8. Substrat entièrement ou partiellement revêtu, caractérisé en ce qu'on utilise comme matière de revêtement un revêtement en poudre selon l'une quelconque des revendications 1 à 6.
EP83201538A 1982-10-29 1983-10-26 Polyester et son utilisation comme revêtement en poudre Expired - Lifetime EP0107888B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83201538T ATE20530T1 (de) 1982-10-29 1983-10-26 Polyester und seine anwendung als pulverfoermiges ueberzugsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL8204205A NL8204205A (nl) 1982-10-29 1982-10-29 Polyester en de toepassing daarvan in poederlak.
NL8204205 1982-10-29

Publications (3)

Publication Number Publication Date
EP0107888A1 EP0107888A1 (fr) 1984-05-09
EP0107888B1 EP0107888B1 (fr) 1986-06-25
EP0107888B2 true EP0107888B2 (fr) 1994-04-06

Family

ID=19840494

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83201538A Expired - Lifetime EP0107888B2 (fr) 1982-10-29 1983-10-26 Polyester et son utilisation comme revêtement en poudre

Country Status (10)

Country Link
US (2) US4471108A (fr)
EP (1) EP0107888B2 (fr)
JP (1) JPS5998129A (fr)
AT (1) ATE20530T1 (fr)
BE (1) BE898099A (fr)
CA (1) CA1216992A (fr)
DE (1) DE3364278D1 (fr)
ES (2) ES526856A0 (fr)
NL (1) NL8204205A (fr)
NO (1) NO159021C (fr)

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GB8609034D0 (en) * 1986-04-14 1986-05-21 Ucb Sa Preparation of polyesters
US4801680A (en) * 1987-12-30 1989-01-31 Ppg Industries, Inc. Hydroxyalkylamide powder coating curing system
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US5177159A (en) * 1989-08-23 1993-01-05 Ciba-Geigy Corporation Polyhydroxy esters containing carboxyl end groups and their use
US5006612A (en) * 1989-10-18 1991-04-09 Cargill, Incorporated Polyesters for powder coating resins using an intermediate having low process viscosity
JP2810500B2 (ja) * 1990-07-03 1998-10-15 日本ペイント株式会社 粉体塗料
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JPH04103678A (ja) * 1990-08-22 1992-04-06 Nippon Paint Co Ltd 粉体塗料組成物
JPH04214771A (ja) * 1990-12-11 1992-08-05 Nippon Ester Co Ltd 粉体塗料用樹脂組成物
US5340909A (en) * 1991-12-18 1994-08-23 Hoechst Celanese Corporation Poly(1,3-propylene terephthalate)
NL9201985A (nl) † 1992-11-13 1994-06-01 Dsm Nv Poederverf op basis van een polymeer met vrije carbonzuurgroepen als bindmiddel en een beta-hydroxyalkylamidegroepen bevattende verbinding als crosslinker.
DE4335845C3 (de) * 1993-10-20 2001-06-13 Inventa Ag Wärmehärtende Beschichtungsmasse, deren Herstellung und Verwendung
DE4401438C2 (de) * 1994-01-19 1997-09-18 Inventa Ag Wärmehärtbares Beschichtungssystem, dessen Herstellung und Verwendung
CN1073603C (zh) 1994-11-28 2001-10-24 日产化学工业株式会社 用于粉末涂料的树脂组合物
WO1997016473A1 (fr) * 1995-11-03 1997-05-09 Union Carbide Chemicals And Plastics Technology Corporation Polyesters et procedes de preparation
US5637654A (en) * 1996-08-12 1997-06-10 Mcwhorter Technologies Low temperature cure carboxyl terminated polyesters
US6020414A (en) * 1996-10-23 2000-02-01 Hoechst Celanese Corporation Method and compositions for toughening polyester resins
US5760161A (en) * 1997-02-10 1998-06-02 Albemarle Corporation Process for making unsaturated, thermosetting, brominated phthalic anhydride/polyol polyester resins
DE19735540C1 (de) 1997-08-16 1999-04-01 Basf Coatings Ag Mit einem Mehrschichtüberzug versehenes Substrat und Verfahren zu dessen Herstellung
DE19850211C1 (de) 1998-10-31 2000-11-23 Basf Coatings Ag Pulverlacke und ihre Verwendung zur Herstellung geräuscharmer Pulverlackbeschichtungen
CN1103355C (zh) * 1999-11-10 2003-03-19 机械工业部广州电器科学研究所 耐候粉末涂料用聚酯树脂的制备方法
US6294610B1 (en) 1999-11-29 2001-09-25 Rohm And Haas Company Coating powders for heat-sensitive substrates
IN190699B (fr) * 2001-02-02 2003-08-16 Sun Pharmaceutical Ind Ltd
US7834127B2 (en) * 2001-07-18 2010-11-16 Eastman Chemical Company Amorphous copolyesters
US20030060596A1 (en) * 2001-07-18 2003-03-27 Turner Sam Richard Amorphous copolyesters
US20040151854A1 (en) * 2003-02-03 2004-08-05 Pecorini Thomas Joseph Extrusion blow molded articles
WO2004083326A1 (fr) * 2003-03-20 2004-09-30 Surface Specialties, S.A. Compositions en poudre thermodurcissables pour revetements
US8846154B2 (en) 2005-06-07 2014-09-30 S.C. Johnson & Son, Inc. Carpet décor and setting solution compositions
US7727289B2 (en) 2005-06-07 2010-06-01 S.C. Johnson & Son, Inc. Composition for application to a surface
US8061269B2 (en) 2008-05-14 2011-11-22 S.C. Johnson & Son, Inc. Multilayer stencils for applying a design to a surface
US8557758B2 (en) 2005-06-07 2013-10-15 S.C. Johnson & Son, Inc. Devices for applying a colorant to a surface
US7776108B2 (en) * 2005-06-07 2010-08-17 S.C. Johnson & Son, Inc. Composition for application to a surface
CA2610730C (fr) * 2005-06-07 2013-04-23 S. C. Johnson & Son, Inc. Procede de neutralisation d'une tache sur une surface
US9096711B2 (en) * 2009-04-29 2015-08-04 Dsm Ip Assets B.V. Powder coating composition comprising a polyester and a crosslinker with oxirane groups providing improved corrosion resistance to a substrate coated therewith
US20110135907A1 (en) * 2009-12-09 2011-06-09 Kiarash Alavi Shooshtari Fiber reinforced composite materials and methods for their manufacture and use
JP5722796B2 (ja) * 2009-12-25 2015-05-27 花王株式会社 保護層転写シート用樹脂組成物
CN108779364B (zh) * 2016-03-30 2021-06-22 埃卡特有限公司 用于粉末涂漆的涂覆有有机粘合剂的效应颜料、以及用于生产所述涂覆的效应颜料的方法及其用途
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DE2935446A1 (de) * 1979-09-01 1981-03-19 Bayer Ag, 5090 Leverkusen Pulverlachbindemittel und verfahren zu ihrer herstellung

Also Published As

Publication number Publication date
US4471108A (en) 1984-09-11
ES8502139A1 (es) 1984-12-16
EP0107888B1 (fr) 1986-06-25
US4528341A (en) 1985-07-09
NO833948L (no) 1984-04-30
BE898099A (nl) 1984-02-15
NO159021B (no) 1988-08-15
ES526856A0 (es) 1984-12-16
ATE20530T1 (de) 1986-07-15
NL8204205A (nl) 1984-05-16
ES535230A0 (es) 1985-05-01
ES8504858A1 (es) 1985-05-01
CA1216992A (fr) 1987-01-20
DE3364278D1 (en) 1986-07-31
EP0107888A1 (fr) 1984-05-09
JPS5998129A (ja) 1984-06-06
NO159021C (no) 1988-11-23

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